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2-Chloropropionic acid



2-Chloropropionic acid
IUPAC name 2-Propanoic acid
Other names α-propanoic acid; α-propanoic acid
Identifiers
CAS number 598-78-7
SMILES CC(Cl)C(O)=O
Properties
Molecular formula C3H4ClO2
Molar mass 108.52 g/mol
Appearance Colorless liquid
Density 1.18 g/mL
Melting point

-13 °C

Boiling point

78 °C at 10 mmHg

Solubility in water Miscible
Viscosity  ? cP at ?°C
Hazards
MSDS External MSDS
Main hazards Very toxic, corrosive
R-phrases R22 R26 R27 R28 R35
S-phrases (S1) (S2) S23 S26 S28 S36 S45
Flash point 101 °C
Related Compounds
Related compounds Propionic acid
chloroacetic acid
Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)

Infobox disclaimer and references

2-Chloropropionic acid is the chemical compound with the formula CH3CHClCO2H. This colorless liquid is the simplest chiral chlorocarboxylic acid, and it is noteworthy for being readily available as a single enantiomer.

Additional recommended knowledge

Preparation and use in organic synthesis

Enantiomerically pure S-2-chloropropionic acid is prepared from alanine via diazotization in hydrochloric acid.[1] Other α-amino acids undergo this reaction.

Reduction of S-2-chloropropionic acid with lithium aluminium hydride affords S-2-chloropropanol, the simplest chloro-alcohol. This alcohol undergoes cyclization upon treatment potassium hydroxide, which causes dehydrohalogenation to give the epoxide, R-methyloxirane.[2]

Safety

In general, α-halocarboxylic acids and their esters are good alkylating agents and should be handled with care. 2-Chloropropionic acid is a neurotoxin.[3]

References

  1. ^ Koppenhoefer, B.; Schurig, V. “S-2-Chloroalkanoic Acids of High Enantiomeric Purity from (S)-2-Amino Acids: (S)-2-Chloropropanoic Acid” Organic Syntheses, Collected Volume 8, p.119 (1993). [1]
  2. ^ Koppenhoefer, B.; Schurig, V. (R)-Alkyloxiranes of Hight Enantiomeric Purity from (S)-2-Chloroalkanoic Acids via (S)-2-Chloro-1-Alkanols: (R)-Methyloxirane” Organic Syntheses, Coll. Vol. 8, p.434 (1993). [2]
  3. ^ Simpson MG, Wyatt I, Jones HB, Gyte AJ, Widdowson PS, Lock EA. (1996). "Neuropathological changes in rat brain following oral administration of 2-chloropropionic acid.". Neurotoxicology 17 (2): 471-80. PMID 8856742.
 
This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "2-Chloropropionic_acid". A list of authors is available in Wikipedia.
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